94376-50-8

Basic information

• Product Name: 10-hydroxy-8-octadecenoic acid
• Synonyms: 10-hydroxy-8-octadecenoic acid
• CAS NO: 94376-50-8
• Molecular Formula: C₁₈H₃₄O₃
• Molecular Weight: 0
• Mol File: 94376-50-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 10-hydroxy-8-octadecenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 10-hydroxy-8-octadecenoic acid(94376-50-8)
• EPA Substance Registry System: 10-hydroxy-8-octadecenoic acid(94376-50-8)

Safety Data

• Hazardous Substances Data: 94376-50-8(Hazardous Substances Data)

Upstream product

• 112-80-1 cis-Octadecenoic acid 

Relevant articles and documents

PpoC from Aspergillus nidulans is a fusion protein with only one active haem

In Aspergillus nidulans Ppos [psi (precocious sexual inducer)-producing oxygenases] are required for the production of so-called psi factors, compounds that control the balance between the sexual and asexual life cycle of the fungus. The genome of A. nidulans harbours three different ppo genes: ppoA, ppoB and ppoC. For all three enzymes two different haem-containing domains are predicted: a fatty acid haem peroxidase/ dioxygenase domain in the N-terminal region and a P450 haem-thiolate domain in the C-terminal region. Whereas PpoA was shown to use both haem domains for its bifunctional catalytic activity (linoleic acid 8-dioxygenation and 8-hydroperoxide isomerization), we found that PpoC apparently only harbours a functional haem peroxidase/dioxygenase domain. Consequently, we observed that PpoC catalyses mainly the dioxygenation of linoleic acid (18:2Δ 9Z,12Z), yielding 10-HPODE (10-hydroperoxyoctadecadienoic acid). No isomerase activity was detected. Additionally, 10-HPODE was converted at lower rates into 10-KODE (10-keto-octadecadienoic acid) and 10-HODE (10-hydroxyoctadecadienoic acid). In parallel, decomposition of 10-HPODE into 10-ODA (10-octadecynoic acid) and volatile C-8 alcohols that are, among other things, responsible for the characteristic mushroom flavour. Besides these principle differences we also found that PpoA and PpoC can convert 8-HPODE and 10-HPODE into the respective epoxy alcohols: 12,13-epoxy-8-HOME (where HOME is hydroxyoctadecenoic acid) and 12,13-epoxy-10-HOME. By using site-directed mutagenesis we demonstrated that both enzymes share a similar mechanism for the oxidation of 18:2Δ9Z,12Z; they both use a conserved tyrosine residue for catalysis and the directed oxygenation at the C-8 and C-10 is most likely controlled by conserved valine/leucine residues in the dioxygenase domain. The Authors Journal compilation